2023 Trending Destinations: Woodstock, Vermont

At LandVest, we have always known that Woodstock, Vermont is a special place to live, work and play. Recently, American Express Travel announced its top ten worldwide trending destinations, which include Woodstock!  

Check out these trending homes in Woodstock: 

Star Hill Farm 

Every aspect of Star Hill Farm is exceptional – the location, land, privacy, the views, and the craftsmanship. The land alone is a mesmerizing 183.7± acre oasis of rolling terrain stonewalls, trails, meadows and pastures, from the valley floor in South Woodstock to the top of Meeting House Hill. From the 11,400 square-foot main house the views across the valley to the mountains are beautiful.

The interior feels relaxed and comfortable while easily accommodating family and friends with its 7 ensuite bedrooms and multiple gathering spaces. A professional grade athletic facility built as a classic gambrel barn with a heated 6-car garage anchors the east wing of the building. The original late 1700’s cape and barn have been completely rebuilt and updated, now a two-bedroom guest house and party barn overlooking the swimming pool. See more here. 

The Lewis Farm 

Sense of place: The classic Vermont farmstead with an iconic big red barn above Green Mountain Horse Association, the Lewis Farm’s 130 acres of hayfields and woodlands span the Kedron Valley hillside just outside the village of South Woodstock.

The legacy of stewardship by the Lewis family started in 1940: tending the land, restoring the spectacular barn and converting its lower level to well-planned stabling, conserving the most visible 30 acres along the road, and epitomizing the sense of community and engagement that characterizes South Woodstock and GMHA. Along with the 3-bedroom brick farmhouse, riding ring, and smokehouse, a light-filled 2-bedroom contemporary takes in the views, and a south-facing studio is set into the hillside. See more here. 

Three Church Street 

A handsome Federal Greek Revival built in 1831 by Joel Eaton, Three Church Street is at the heart of the picturesque village of Woodstock, voted the most beautiful town in America by Conde Nast Traveler. The house is rumored to have been a stop on the Underground Railroad and local lore has it that General Lafayette slept here. The east wing was added in the 1860s and was a recovery home for civil war veterans.

Set on just under two acres with 249 feet on the Ottauquechee River, the exquisitely renovated house has maintained its historical integrity while adding modern amenities such as en-suite bedrooms and air conditioning. The two-acre property has been meticulously maintained and is in exceptional, move-in condition. It comes completely furnished and includes an in-law apartment and guest apartment.  

An expansive porch looks out over a private back lawn that gently slopes down to the river with views of Mt. Tom. The outdoor areas have a sense of space with the added pleasures of perennial gardens, a heated pool and fire pit. See more here. 

Hidden Ridge Farm 

Room to roam, big views, privacy, space for everyone: This exceptional Vermont recreational retreat on 75.8± private acres has sweeping vistas to the south. The 6-bedroom, 5-bath residence is set up to provide suites for privacy, as well as comfortable gathering spaces opening to the views of meadows on to layered hills and distant mountains.

Extensive recreational amenities include an in-ground heated pool, clay tennis court, sledding hill and, of course, the beautiful countryside to explore. Horses and their people will appreciate the 85 x 150 heated and sprinklered indoor arena complex with a 5-stall stable, viewing area with kitchen and office, ample hay storage, 2-bedroom apartment, 80 x 100 outdoor arena, 6-stall field barn and post & rail fenced pastures. See more here. 

Contact us below to learn about the above listings or our exclusive private listings in the Woodstock area.  

Story Jenks
Principal, Regional Managing Broker
Dia Jenks
Luxury Real Estate Agent
Christopher Lang
Regional Manager, Upper Valley